Trifluoroacetic acid → HCID 117872299, compound

HRID 530649Notes

Reaction equation

HRID 530649 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:22][O:21][C:18]1[N:17]=[CH:16][C:15]([CH2:14][C@H:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117870842HCID 117870842, compound

Product 1

HCID 117872299HCID 117872299, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(R)-2-(6-Methoxy-pyridin-3-ylmethyl)-morpholine-4-carboxylic acid tert-butyl ester (194 mg, 0.63 mmol) was dissolved in dichloromethane (2 mL), cooled to 0° C. and treated with TFA (1 mL). The reaction was stirred at room temperature for 2 h. The reaction mixture was concentrated. The residue was taken up in dichloromethane and extracted with 1M NaOH. The mixture was extracted 3 times with dichloromethane. The combined organic phase was washed with brine, dried over MgSO4 and concentrated to afford (R)-2-(6-methoxy-pyridin-3-ylmethyl)-morpholine (130 mg, 99%) as a light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.52-2.63 (m, 2H) 2.65-2.75 (m, 1H) 2.75-2.81 (m, 1H) 2.81-2.91 (m, 2H) 3.49-3.63 (m, 2H) 3.85 (ddd, J=11.28, 3.22, 1.34 Hz, 1H) 3.91 (s, 3H) 6.68 (d, J=8.33 Hz, 1H) 7.44 (dd, J=8.60, 2.42 Hz, 1H) 7.99 (d, J=2.15 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with 1M NaOH
  3. extractionThe mixture was extracted 3 times with dichloromethane
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ba2a7e1ae0b4fea8f3c4dec2cd261e3
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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